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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-05-17 01:22:40 UTC
Update Date2021-09-14 15:19:06 UTC
HMDB IDHMDB0060464
Secondary Accession Numbers
  • HMDB60464
Metabolite Identification
Common NameCodeine-6-glucuronide
DescriptionCodeine-6-glucuronide belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. During its metabolism, codeine is conjugated with glucuronic acid by the enzyme UDP-Glucuronosyltransferase-2B7 (UGT2B7) to form codeine-6-glucuronide. Codeine-6-glucuronide is a very strong basic compound (based on its pKa). codeine-6-glucuronide and uridine 5'-diphosphate can be biosynthesized from codeine and uridine diphosphate glucuronic acid through the action of the enzyme UDP-glucuronosyltransferase 2B7. In humans, codeine-6-glucuronide is involved in codeine metabolism pathway. C6G exhibits decreased immunosuppressive effects compared to codeine. Codeine-6-glucuronide (C6G) is a major active metabolite of codeine and may be responsible for as much as 60% of the analgesic effects of codeine.
Structure
Data?1563866063
SynonymsNot Available
Chemical FormulaC24H29NO9
Average Molecular Weight475.4884
Monoisotopic Molecular Weight475.184231531
IUPAC Name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraen-14-yl]oxy}oxane-2-carboxylic acid
Traditional Namecodeine-6-glucuronide
CAS Registry Number20736-11-2
SMILES
[H][C@]12C=C[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4OC
InChI Identifier
InChI=1S/C24H29NO9/c1-25-8-7-24-11-4-6-14(32-23-18(28)16(26)17(27)20(34-23)22(29)30)21(24)33-19-13(31-2)5-3-10(15(19)24)9-12(11)25/h3-6,11-12,14,16-18,20-21,23,26-28H,7-9H2,1-2H3,(H,29,30)/t11-,12+,14-,16-,17-,18+,20-,21-,23+,24-/m0/s1
InChI KeyCRWVOYRJXPDBPM-HSCJLHHPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • O-glucuronide
  • 1-o-glucuronide
  • Phenanthrene
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Tetralin
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Aralkylamine
  • Hydroxy acid
  • Oxane
  • Monosaccharide
  • Piperidine
  • Benzenoid
  • Pyran
  • Amino acid or derivatives
  • Amino acid
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Polyol
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point248-250°Chttp://www.buyersguidechem.com/cas_supplier/20736-11-2.html
Boiling PointNot AvailableNot Available
Water Solubility0Toronto Research Chemicals, 2013
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.31 g/LALOGPS
logP10(-0.23) g/LALOGPS
logP10(-2.8) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Acidic)2.87ChemAxon
pKa (Strongest Basic)9.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area138.15 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity116.89 m³·mol⁻¹ChemAxon
Polarizability47.27 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Codeine-6-glucuronide[H][C@]12C=C[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4OC4738.4Standard polar33892256
Codeine-6-glucuronide[H][C@]12C=C[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4OC3622.6Standard non polar33892256
Codeine-6-glucuronide[H][C@]12C=C[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4OC3871.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Codeine-6-glucuronide,1TMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C3693.3Semi standard non polar33892256
Codeine-6-glucuronide,1TMS,isomer #2COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C3705.3Semi standard non polar33892256
Codeine-6-glucuronide,1TMS,isomer #3COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C3692.9Semi standard non polar33892256
Codeine-6-glucuronide,1TMS,isomer #4COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C3644.5Semi standard non polar33892256
Codeine-6-glucuronide,2TMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C3635.5Semi standard non polar33892256
Codeine-6-glucuronide,2TMS,isomer #2COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C3674.2Semi standard non polar33892256
Codeine-6-glucuronide,2TMS,isomer #3COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C3664.3Semi standard non polar33892256
Codeine-6-glucuronide,2TMS,isomer #4COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C3632.6Semi standard non polar33892256
Codeine-6-glucuronide,2TMS,isomer #5COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C3664.4Semi standard non polar33892256
Codeine-6-glucuronide,2TMS,isomer #6COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C3622.0Semi standard non polar33892256
Codeine-6-glucuronide,3TMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C3637.7Semi standard non polar33892256
Codeine-6-glucuronide,3TMS,isomer #2COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C3633.5Semi standard non polar33892256
Codeine-6-glucuronide,3TMS,isomer #3COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C3658.9Semi standard non polar33892256
Codeine-6-glucuronide,3TMS,isomer #4COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C3623.9Semi standard non polar33892256
Codeine-6-glucuronide,4TMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C3644.2Semi standard non polar33892256
Codeine-6-glucuronide,1TBDMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C3919.5Semi standard non polar33892256
Codeine-6-glucuronide,1TBDMS,isomer #2COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C3937.7Semi standard non polar33892256
Codeine-6-glucuronide,1TBDMS,isomer #3COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C3923.0Semi standard non polar33892256
Codeine-6-glucuronide,1TBDMS,isomer #4COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C3887.5Semi standard non polar33892256
Codeine-6-glucuronide,2TBDMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C4091.6Semi standard non polar33892256
Codeine-6-glucuronide,2TBDMS,isomer #2COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C4111.8Semi standard non polar33892256
Codeine-6-glucuronide,2TBDMS,isomer #3COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C4111.9Semi standard non polar33892256
Codeine-6-glucuronide,2TBDMS,isomer #4COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C4096.4Semi standard non polar33892256
Codeine-6-glucuronide,2TBDMS,isomer #5COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C4107.1Semi standard non polar33892256
Codeine-6-glucuronide,2TBDMS,isomer #6COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C4089.6Semi standard non polar33892256
Codeine-6-glucuronide,3TBDMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C4256.5Semi standard non polar33892256
Codeine-6-glucuronide,3TBDMS,isomer #2COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C4268.9Semi standard non polar33892256
Codeine-6-glucuronide,3TBDMS,isomer #3COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C4279.6Semi standard non polar33892256
Codeine-6-glucuronide,3TBDMS,isomer #4COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C4260.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Codeine-6-glucuronide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9202300000-c0e5abf76f3d3777bf712017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Codeine-6-glucuronide GC-MS (3 TMS) - 70eV, Positivesplash10-004i-5251029000-7a0f671ad644403d77042017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Codeine-6-glucuronide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine-6-glucuronide 10V, Positive-QTOFsplash10-0zi0-0156900000-94e266093e29f563d4122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine-6-glucuronide 20V, Positive-QTOFsplash10-0ue9-0189100000-506af8b6b31a10be8b3e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine-6-glucuronide 40V, Positive-QTOFsplash10-001l-1191000000-97b95309ab6cb729c9272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine-6-glucuronide 10V, Negative-QTOFsplash10-00dj-2240900000-97f310bd2d4e910d53862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine-6-glucuronide 20V, Negative-QTOFsplash10-000t-1290300000-addb13b052bca1e8d8cc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine-6-glucuronide 40V, Negative-QTOFsplash10-001m-3190000000-1a066b69fdc8045d75922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine-6-glucuronide 10V, Positive-QTOFsplash10-001i-0091800000-f683f5fbf7057a4763772021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine-6-glucuronide 20V, Positive-QTOFsplash10-001i-0256900000-c792ae5e958b1756378f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine-6-glucuronide 40V, Positive-QTOFsplash10-01q9-6498500000-ff04bfeeb8802cc45c222021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine-6-glucuronide 10V, Negative-QTOFsplash10-00di-0010900000-f61069a4327f438acbc52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine-6-glucuronide 20V, Negative-QTOFsplash10-0002-5984700000-0a2873e05408ba63e5be2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine-6-glucuronide 40V, Negative-QTOFsplash10-059t-9373200000-b8019fef538f241a652d2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Microsomes
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot Available
collected 0–6 h after oral intake of 60 mg of codeine
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedArrested for driving under the influence of drugs. details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specifiedfemoral vein blood in a typical case of fatal heroin overdose. details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedFemale
Heroine addict
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16577
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCodeine-6-glucuronide
METLIN IDNot Available
PubChem Compound5489029
PDB IDNot Available
ChEBI ID80580
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSrinivasan, Vinayak; Wielbo, Donna; Simpkins, James; Karlix, Janet; Sloan, Kenneth; Tebbett, Ian, 1996: Analgesic and immunomodulatory effects of codeine and codeine 6-glucuronide. Pharmaceutical Research (new York). 13(2): 296-300
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Murphy CM, Huestis MA: LC-ESI-MS/MS analysis for the quantification of morphine, codeine, morphine-3-beta-D-glucuronide, morphine-6-beta-D-glucuronide, and codeine-6-beta-D-glucuronide in human urine. J Mass Spectrom. 2005 Nov;40(11):1412-6. [PubMed:16258895 ]
  2. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  3. Srinivasan V, Wielbo D, Tebbett IR: Analgesic effects of codeine-6-glucuronide after intravenous administration. Eur J Pain. 1997;1(3):185-90. [PubMed:15102399 ]
  4. Vree TB, van Dongen RT, Koopman-Kimenai PM: Codeine analgesia is due to codeine-6-glucuronide, not morphine. Int J Clin Pract. 2000 Jul-Aug;54(6):395-8. [PubMed:11092114 ]
  5. Raungrut P, Uchaipichat V, Elliot DJ, Janchawee B, Somogyi AA, Miners JO: In vitro-in vivo extrapolation predicts drug-drug interactions arising from inhibition of codeine glucuronidation by dextropropoxyphene, fluconazole, ketoconazole, and methadone in humans. J Pharmacol Exp Ther. 2010 Aug;334(2):609-18. doi: 10.1124/jpet.110.167916. Epub 2010 May 18. [PubMed:20484152 ]
  6. Bogusz MJ, Maier RD, Erkens M, Driessen S: Determination of morphine and its 3- and 6-glucuronides, codeine, codeine-glucuronide and 6-monoacetylmorphine in body fluids by liquid chromatography atmospheric pressure chemical ionization mass spectrometry. J Chromatogr B Biomed Sci Appl. 1997 Dec 5;703(1-2):115-27. [PubMed:9448068 ]

Only showing the first 10 proteins. There are 18 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT2B10
Uniprot ID:
P36537
Molecular weight:
60773.485
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:
UGT2B15
Uniprot ID:
P54855
Molecular weight:
61035.815
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Molecular weight:
60771.605
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Molecular weight:
59741.035
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails

Only showing the first 10 proteins. There are 18 proteins in total.